Method for producing aldehyde compound or ketone compound by using microreactor

Abstract

The method for producing an aldehyde or ketone compound from a corresponding primary or secondary alcohol at relatively high temperature within a short time with a high yield including a step (1) of reacting a sulfoxide compound with an activating agent to produce an activation reaction product; a step (2) of reacting the activation reaction product with a primary or secondary alcohol to produce an alkoxysulfonium salt; and a step (3) of reacting the reaction product with a base to produce an aldehyde or ketone; wherein at least one of the steps, preferably the step (1) and step (2), are carried out by using a microreactor.

1. A method for producing an aldehyde or ketone compound by using a microreactor, comprising (1) mixing a liquid containing a sulfoxide compound with a liquid containing an activating agent for the sulfoxide compound to cause a reaction with each other and produce an activation reaction product of the sulfoxide compound; (2) mixing a liquid containing the activation reaction product of the sulfoxide compound with a liquid containing at least one member selected from primary and secondary alkyl alcohols to cause a reaction with each other and prepare a liquid containing an alkoxysulfonium salt; and (3) mixing the resulting liquid containing an alkoxysulfonium salt with a basic compound-containing liquid to cause a reaction with each other and prepare a liquid containing an aldehyde or ketone compound corresponding to the alkyl alcohol, wherein at least one of (1), (2) and (3) is carried out by using a microreactor. 
     
     
       2. The method according to  claim 1 , wherein the microreactor comprises two liquid-introducing channels having a fine cross-sectional profile for introducing two type of liquids; one micromixer portion for mixing and reacting two kinds of liquids introduced, with each other having a fine cross-sectional profile and connected to the liquid introducing channel; and one liquid discharging channel for discharging a reaction product liquid from the micromixer portion, having a fine cross-sectional profile. 
     
     
       3. The method according to  claim 2 , wherein two steps connected to each other are carried out by using a microreactor and a liquid discharging channel of a rector of an upstream step and a liquid introducing channel of a reactor of a downstream step connected to the upstream step, are connected with each other through a connecting capillary tube. 
     
     
       4. The method according to  claim 1 , wherein (1) and (2) are carried out in the microreactor. 
     
     
       5. The method according to  claim 2 , wherein the temperature of the liquids in the micromixer portion and the liquid discharging channel of the microreactor is adjusted to a desired value. 
     
     
       6. The method according to  claim 3 , wherein the temperature of the liquids in the connecting capillary tube is adjusted to a desired value. 
     
     
       7. The method according to  claim 2 , wherein the cross-sectional area of the liquid introducing channel, that of the liquid micromixer portion and that of the liquid discharging channel in the microreactor, are respectively, about 0.7 μm 2  to about 1 mm 2 , about 0.7 μm 2  to about 1 mm 2  and about 0.7 μm 2  to about 1 mm 2 . 
     
     
       8. The method according to  claim 2 , wherein a major diameter/minor diameter ratio of the cross section of the liquid introducing channel, the liquid micromixer portion and the liquid discharging channel in the microreactor, is 1 or more and the minor diameter is within a range from about 1 μm to about 1 mm. 
     
     
       9. The method according to  claim 1 , wherein, in the microreactor, the flow rate of the liquid to be discharged from the liquid micromixer is adjusted so that two kinds of liquids mixed with each other can be reacted to each other in the microreactor with a desired mixing efficiency and a desired retention time. 
     
     
       10. The method according to  claim 1 , wherein the residence time of the liquid in the microreactor is adjusted to within a range from about 0.001 to about 60 seconds. 
     
     
       11. The method according to  claim 2 , wherein (1) is carried out using a microreactor and the residence time of a mixed reaction solution of the sulfoxide compound-containing liquid with an activating agent-containing liquid in a portion of the microreactor between the inlet of the micromixer portion and the inlet of the reactor for (2) is in the range of from about 0.001 to about 60 seconds. 
     
     
       12. The method according to  claim 1 , wherein (1) is carried out in the microreactor and the reaction temperature in (1) is in the range of from about −80 to about +50° C. 
     
     
       13. The method according to  claim 1 , wherein (2) is carried out in the microreactor and the mixing reaction temperature in (2) is in the range of from about −80 to about +50° C. 
     
     
       14. The method according to  claim 1 , wherein the sulfoxide compound is selected from a dialkyl sulfoxide. 
     
     
       15. The method according to  claim 1 , wherein dimethyl sulfoxide is used as the dialkyl sulfoxide. 
     
     
       16. The method according to  claim 1 , wherein the activating agent for a sulfoxide compound is selected from the group consisting of acetic anhydride, oxalyl chloride, trifluoroacetic anhydride, trifluoromethanesulfonic anhydride, diphosphorus pentaoxide, chlorine, benzoyl chloride, acetyl chloride, methanesulfonyl chloride, p-toluenesulfonyl chloride, sulfur trioxide-pyridine complex and 2,4,6-trichloro-1,3,5-triazine. 
     
     
       17. The method according to  claim 1 , wherein the primary and secondary alcohols are selected from saturated and unsaturated C 1 -C 20  aliphatic primary and secondary alcohols, or saturated and unsaturated aliphatic primary and secondary alcohols having an alicyclic aromatic hydrocarbon group, and saturated and unsaturated primary and secondary alcohols having a heterocyclic group. 
     
     
       18. The method according to  claim 1 , wherein the basic compound is selected from organic amine compounds. 
     
     
       19. The method according to  claim 18 , wherein the organic amine compound is selected from trialkylamines. 
     
     
       20. The method according to  claim 1 , wherein a molar ratio of the sulfoxide compound to be supplied in (1) to the primary or secondary alcohol to be supplied in (2) is within a range of from 1:1 to 20:1. 
     
     
       21. The method according to  claim 1 , wherein a molar ratio of the activating agent for a sulfoxide compound to be supplied in (1) to the primary or secondary alcohol to be supplied in (2) is within a range of from 1:1 to 2:1. 
     
     
       22. The method according to  claim 1 , wherein a molar amount of the base compound to be supplied in (3) is 2 to 20 times the molar amount of the primary or secondary alcohol to be supplied in (2). 
     
     
       23. The method according to  claim 1 , further comprising isolating the target aldehyde or ketone compound from the aldehyde or ketone compound-containing liquid prepared in (3).